JP2007284434A - キノキサリン誘導体、およびキノキサリン誘導体を用いた発光素子、発光装置、電子機器 - Google Patents
キノキサリン誘導体、およびキノキサリン誘導体を用いた発光素子、発光装置、電子機器 Download PDFInfo
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- JP2007284434A JP2007284434A JP2007073638A JP2007073638A JP2007284434A JP 2007284434 A JP2007284434 A JP 2007284434A JP 2007073638 A JP2007073638 A JP 2007073638A JP 2007073638 A JP2007073638 A JP 2007073638A JP 2007284434 A JP2007284434 A JP 2007284434A
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- carbon atoms
- hydrogen atom
- alkyl group
- general formula
- aryl group
- Prior art date
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- 125000001567 quinoxalinyl group Chemical class N1=C(C=NC2=CC=CC=C12)* 0.000 title claims abstract 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 442
- 125000003118 aryl group Chemical group 0.000 claims description 217
- 125000000217 alkyl group Chemical group 0.000 claims description 191
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 185
- 239000000126 substance Substances 0.000 claims description 78
- 229910052799 carbon Inorganic materials 0.000 claims description 43
- 125000000732 arylene group Chemical group 0.000 claims description 42
- 125000001424 substituent group Chemical group 0.000 claims description 25
- 150000001721 carbon Chemical group 0.000 claims description 24
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 15
- 125000004429 atom Chemical group 0.000 claims description 6
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 claims description 5
- 238000006467 substitution reaction Methods 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 150000002894 organic compounds Chemical class 0.000 abstract description 40
- 239000010410 layer Substances 0.000 description 186
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 129
- 150000003252 quinoxalines Chemical class 0.000 description 127
- 239000000243 solution Substances 0.000 description 64
- 230000015572 biosynthetic process Effects 0.000 description 57
- 238000003786 synthesis reaction Methods 0.000 description 55
- 238000005481 NMR spectroscopy Methods 0.000 description 51
- 239000000758 substrate Substances 0.000 description 50
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 48
- 239000010408 film Substances 0.000 description 45
- 239000010409 thin film Substances 0.000 description 45
- 238000000862 absorption spectrum Methods 0.000 description 44
- 150000001875 compounds Chemical class 0.000 description 44
- 238000000034 method Methods 0.000 description 42
- CUJRVFIICFDLGR-UHFFFAOYSA-N acetylacetonate Chemical compound CC(=O)[CH-]C(C)=O CUJRVFIICFDLGR-UHFFFAOYSA-N 0.000 description 41
- 238000000295 emission spectrum Methods 0.000 description 37
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 35
- 239000000463 material Substances 0.000 description 35
- 239000007787 solid Substances 0.000 description 34
- 230000005284 excitation Effects 0.000 description 32
- 238000001704 evaporation Methods 0.000 description 29
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 29
- 239000002131 composite material Substances 0.000 description 28
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 26
- 238000010521 absorption reaction Methods 0.000 description 26
- 229910052757 nitrogen Inorganic materials 0.000 description 25
- 238000006722 reduction reaction Methods 0.000 description 25
- 230000005525 hole transport Effects 0.000 description 24
- 238000006243 chemical reaction Methods 0.000 description 23
- 239000000706 filtrate Substances 0.000 description 23
- 238000005259 measurement Methods 0.000 description 21
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 238000007254 oxidation reaction Methods 0.000 description 19
- 239000010453 quartz Substances 0.000 description 19
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000002347 injection Methods 0.000 description 18
- 239000007924 injection Substances 0.000 description 18
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 18
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 18
- 229910052744 lithium Inorganic materials 0.000 description 17
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 16
- 230000008020 evaporation Effects 0.000 description 16
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 229910052782 aluminium Inorganic materials 0.000 description 15
- 238000002484 cyclic voltammetry Methods 0.000 description 15
- 238000010438 heat treatment Methods 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 14
- 230000006870 function Effects 0.000 description 14
- ULNBZCYCZMUKHH-UHFFFAOYSA-N C1=CC=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=C(C=2C(=NC3=CC=CC=C3N=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N1C2=CC=CC=C2C2=CC=CC=C21)C1=CC=C(C=2C(=NC3=CC=CC=C3N=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 ULNBZCYCZMUKHH-UHFFFAOYSA-N 0.000 description 13
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 13
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 13
- 230000009477 glass transition Effects 0.000 description 13
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 13
- 235000019341 magnesium sulphate Nutrition 0.000 description 13
- 230000009467 reduction Effects 0.000 description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- 238000000151 deposition Methods 0.000 description 12
- 125000004556 carbazol-9-yl group Chemical group C1=CC=CC=2C3=CC=CC=C3N(C12)* 0.000 description 11
- 230000008859 change Effects 0.000 description 11
- 150000002484 inorganic compounds Chemical class 0.000 description 11
- 229910010272 inorganic material Inorganic materials 0.000 description 11
- 239000012044 organic layer Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 11
- 230000002194 synthesizing effect Effects 0.000 description 11
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 10
- FRQPRDRLNADTJT-UHFFFAOYSA-N C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C(=NC3=CC=CC=C3N=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C(=NC3=CC=CC=C3N=2)C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C=C3C4=CC=CC=C4N(C=4C=CC=CC=4)C3=CC=2)C=C1 FRQPRDRLNADTJT-UHFFFAOYSA-N 0.000 description 10
- 238000003775 Density Functional Theory Methods 0.000 description 10
- 125000005595 acetylacetonate group Chemical group 0.000 description 10
- -1 aromatic amine compound Chemical class 0.000 description 10
- 239000012298 atmosphere Substances 0.000 description 10
- 238000004364 calculation method Methods 0.000 description 10
- 230000000052 comparative effect Effects 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 229910052740 iodine Inorganic materials 0.000 description 10
- 239000011630 iodine Substances 0.000 description 10
- MILUBEOXRNEUHS-UHFFFAOYSA-N iridium(3+) Chemical compound [Ir+3] MILUBEOXRNEUHS-UHFFFAOYSA-N 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 10
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 9
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 9
- 229910052794 bromium Inorganic materials 0.000 description 9
- 229910052736 halogen Inorganic materials 0.000 description 9
- 150000002367 halogens Chemical class 0.000 description 9
- 229910052751 metal Inorganic materials 0.000 description 9
- 239000002184 metal Substances 0.000 description 9
- FGKQIVRJPLCYCP-UHFFFAOYSA-N n,9-diphenyl-n-[4-(3-phenylquinoxalin-2-yl)phenyl]carbazol-3-amine Chemical compound C1=CC=CC=C1N(C=1C=C2C3=CC=CC=C3N(C=3C=CC=CC=3)C2=CC=1)C1=CC=C(C=2C(=NC3=CC=CC=C3N=2)C=2C=CC=CC=2)C=C1 FGKQIVRJPLCYCP-UHFFFAOYSA-N 0.000 description 9
- 238000007740 vapor deposition Methods 0.000 description 9
- VFUDMQLBKNMONU-UHFFFAOYSA-N 9-[4-(4-carbazol-9-ylphenyl)phenyl]carbazole Chemical group C12=CC=CC=C2C2=CC=CC=C2N1C1=CC=C(C=2C=CC(=CC=2)N2C3=CC=CC=C3C3=CC=CC=C32)C=C1 VFUDMQLBKNMONU-UHFFFAOYSA-N 0.000 description 8
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 8
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 8
- AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 8
- 239000004973 liquid crystal related substance Substances 0.000 description 8
- 229910044991 metal oxide Inorganic materials 0.000 description 8
- 150000004706 metal oxides Chemical class 0.000 description 8
- DZRDATNLTUIPAY-UHFFFAOYSA-N n,9-diphenylcarbazol-3-amine Chemical compound C=1C=C2N(C=3C=CC=CC=3)C3=CC=CC=C3C2=CC=1NC1=CC=CC=C1 DZRDATNLTUIPAY-UHFFFAOYSA-N 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 8
- 238000004544 sputter deposition Methods 0.000 description 8
- FKHIFSZMMVMEQY-UHFFFAOYSA-N talc Chemical compound [Mg+2].[O-][Si]([O-])=O FKHIFSZMMVMEQY-UHFFFAOYSA-N 0.000 description 8
- TVIVIEFSHFOWTE-UHFFFAOYSA-K tri(quinolin-8-yloxy)alumane Chemical compound [Al+3].C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1.C1=CN=C2C([O-])=CC=CC2=C1 TVIVIEFSHFOWTE-UHFFFAOYSA-K 0.000 description 8
- 238000000870 ultraviolet spectroscopy Methods 0.000 description 8
- CGSJDTBQZLZMLH-UHFFFAOYSA-N 1-n,1-n,4-n-triphenyl-4-n-[4-(3-phenylquinoxalin-2-yl)phenyl]benzene-1,4-diamine Chemical compound C1=CC=CC=C1N(C=1C=CC(=CC=1)N(C=1C=CC=CC=1)C=1C=CC(=CC=1)C=1C(=NC2=CC=CC=C2N=1)C=1C=CC=CC=1)C1=CC=CC=C1 CGSJDTBQZLZMLH-UHFFFAOYSA-N 0.000 description 7
- 230000006866 deterioration Effects 0.000 description 7
- 125000002524 organometallic group Chemical group 0.000 description 7
- 230000003647 oxidation Effects 0.000 description 7
- 229910052697 platinum Inorganic materials 0.000 description 7
- OLJCVZUGBZYQOD-UHFFFAOYSA-N 2-(4-bromophenyl)-3-phenylquinoxaline Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2N=C1C1=CC=CC=C1 OLJCVZUGBZYQOD-UHFFFAOYSA-N 0.000 description 6
- XSDKKRKTDZMKCH-UHFFFAOYSA-N 9-(4-bromophenyl)carbazole Chemical compound C1=CC(Br)=CC=C1N1C2=CC=CC=C2C2=CC=CC=C21 XSDKKRKTDZMKCH-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical group C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 6
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 6
- AMWRITDGCCNYAT-UHFFFAOYSA-L hydroxy(oxo)manganese;manganese Chemical compound [Mn].O[Mn]=O.O[Mn]=O AMWRITDGCCNYAT-UHFFFAOYSA-L 0.000 description 6
- 229910003437 indium oxide Inorganic materials 0.000 description 6
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical compound [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 description 6
- 239000012212 insulator Substances 0.000 description 6
- 229910052741 iridium Inorganic materials 0.000 description 6
- GKOZUEZYRPOHIO-UHFFFAOYSA-N iridium atom Chemical compound [Ir] GKOZUEZYRPOHIO-UHFFFAOYSA-N 0.000 description 6
- 239000011777 magnesium Substances 0.000 description 6
- IBHBKWKFFTZAHE-UHFFFAOYSA-N n-[4-[4-(n-naphthalen-1-ylanilino)phenyl]phenyl]-n-phenylnaphthalen-1-amine Chemical group C1=CC=CC=C1N(C=1C2=CC=CC=C2C=CC=1)C1=CC=C(C=2C=CC(=CC=2)N(C=2C=CC=CC=2)C=2C3=CC=CC=C3C=CC=2)C=C1 IBHBKWKFFTZAHE-UHFFFAOYSA-N 0.000 description 6
- QGLKJKCYBOYXKC-UHFFFAOYSA-N nonaoxidotritungsten Chemical compound O=[W]1(=O)O[W](=O)(=O)O[W](=O)(=O)O1 QGLKJKCYBOYXKC-UHFFFAOYSA-N 0.000 description 6
- 238000000746 purification Methods 0.000 description 6
- 239000004065 semiconductor Substances 0.000 description 6
- 229910052814 silicon oxide Inorganic materials 0.000 description 6
- 238000000859 sublimation Methods 0.000 description 6
- 230000008022 sublimation Effects 0.000 description 6
- 238000000967 suction filtration Methods 0.000 description 6
- 229910001930 tungsten oxide Inorganic materials 0.000 description 6
- 239000011787 zinc oxide Substances 0.000 description 6
- UKSZBOKPHAQOMP-SVLSSHOZSA-N (1e,4e)-1,5-diphenylpenta-1,4-dien-3-one;palladium Chemical compound [Pd].C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1.C=1C=CC=CC=1\C=C\C(=O)\C=C\C1=CC=CC=C1 UKSZBOKPHAQOMP-SVLSSHOZSA-N 0.000 description 5
- WATVCMJLZPTSSS-UHFFFAOYSA-N 2,3-bis(4-bromophenyl)quinoxaline Chemical compound C1=CC(Br)=CC=C1C1=NC2=CC=CC=C2N=C1C1=CC=C(Br)C=C1 WATVCMJLZPTSSS-UHFFFAOYSA-N 0.000 description 5
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 5
- NRTOMJZYCJJWKI-UHFFFAOYSA-N Titanium nitride Chemical compound [Ti]#N NRTOMJZYCJJWKI-UHFFFAOYSA-N 0.000 description 5
- 229910045601 alloy Inorganic materials 0.000 description 5
- 239000000956 alloy Substances 0.000 description 5
- UFVXQDWNSAGPHN-UHFFFAOYSA-K bis[(2-methylquinolin-8-yl)oxy]-(4-phenylphenoxy)alumane Chemical compound [Al+3].C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC=C([O-])C2=NC(C)=CC=C21.C1=CC([O-])=CC=C1C1=CC=CC=C1 UFVXQDWNSAGPHN-UHFFFAOYSA-K 0.000 description 5
- 238000010549 co-Evaporation Methods 0.000 description 5
- 230000008021 deposition Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 238000001914 filtration Methods 0.000 description 5
- 238000004770 highest occupied molecular orbital Methods 0.000 description 5
- 239000011159 matrix material Substances 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 5
- 238000005192 partition Methods 0.000 description 5
- 238000001420 photoelectron spectroscopy Methods 0.000 description 5
- 238000007789 sealing Methods 0.000 description 5
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 5
- 238000001771 vacuum deposition Methods 0.000 description 5
- KUBSCXXKQGDPPD-UHFFFAOYSA-N 3-bromo-9-phenylcarbazole Chemical compound C12=CC=CC=C2C2=CC(Br)=CC=C2N1C1=CC=CC=C1 KUBSCXXKQGDPPD-UHFFFAOYSA-N 0.000 description 4
- AZFHXIBNMPIGOD-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one iridium Chemical compound [Ir].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O AZFHXIBNMPIGOD-UHFFFAOYSA-N 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 4
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 0 CCNIN(*)*c1nc(c(*)c(*)c(*)c2*)c2nc1*N(N)[Al] Chemical compound CCNIN(*)*c1nc(c(*)c(*)c(*)c2*)c2nc1*N(N)[Al] 0.000 description 4
- 238000004057 DFT-B3LYP calculation Methods 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- XJHCXCQVJFPJIK-UHFFFAOYSA-M caesium fluoride Chemical compound [F-].[Cs+] XJHCXCQVJFPJIK-UHFFFAOYSA-M 0.000 description 4
- 150000001716 carbazoles Chemical class 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 230000001413 cellular effect Effects 0.000 description 4
- 238000000354 decomposition reaction Methods 0.000 description 4
- 230000005281 excited state Effects 0.000 description 4
- 238000004768 lowest unoccupied molecular orbital Methods 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 4
- 239000000565 sealant Substances 0.000 description 4
- 229910052710 silicon Inorganic materials 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 230000007704 transition Effects 0.000 description 4
- BWHDROKFUHTORW-UHFFFAOYSA-N tritert-butylphosphane Chemical compound CC(C)(C)P(C(C)(C)C)C(C)(C)C BWHDROKFUHTORW-UHFFFAOYSA-N 0.000 description 4
- 229910001935 vanadium oxide Inorganic materials 0.000 description 4
- REKFALFAMJBFCR-UHFFFAOYSA-N 1-(4-bromophenyl)-2-phenylethane-1,2-dione Chemical compound C1=CC(Br)=CC=C1C(=O)C(=O)C1=CC=CC=C1 REKFALFAMJBFCR-UHFFFAOYSA-N 0.000 description 3
- XLHCHVUFUPJPEO-UHFFFAOYSA-N 1-bromo-4-(2-phenylethynyl)benzene Chemical group C1=CC(Br)=CC=C1C#CC1=CC=CC=C1 XLHCHVUFUPJPEO-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 3
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 3
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- OYQCBJZGELKKPM-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O-2].[Zn+2].[O-2].[In+3] OYQCBJZGELKKPM-UHFFFAOYSA-N 0.000 description 1
- YVTHLONGBIQYBO-UHFFFAOYSA-N zinc indium(3+) oxygen(2-) Chemical compound [O--].[Zn++].[In+3] YVTHLONGBIQYBO-UHFFFAOYSA-N 0.000 description 1
- GWDUZCIBPDVBJM-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzothiazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)SC2=CC=CC=C2N1 GWDUZCIBPDVBJM-UHFFFAOYSA-L 0.000 description 1
- QEPMORHSGFRDLW-UHFFFAOYSA-L zinc;2-(2-hydroxyphenyl)-3h-1,3-benzoxazole-2-carboxylate Chemical compound [Zn+2].OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1.OC1=CC=CC=C1C1(C([O-])=O)OC2=CC=CC=C2N1 QEPMORHSGFRDLW-UHFFFAOYSA-L 0.000 description 1
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Abstract
Description
C.W.タン、外1名、アプライド フィジクス レターズ、vol.51、No.12、913−915(1987) チハヤ アダチ、外3名、ジャパニーズ ジャーナル オブ アプライド フィジクス、vol.27、No.2、L269−L271(1988)
本実施の形態では、本発明のキノキサリン誘導体について説明する。
本発明のキノキサリン誘導体を用いた発光素子の一態様について図1(A)を用いて以下に説明する。
本実施の形態では、実施の形態2で示した構成と異なる構成の発光素子について説明する。
本実施の形態では、実施の形態2および実施の形態3で示した構成と異なる構成の発光素子について説明する。
本実施の形態は、本発明に係る複数の発光ユニットを積層した構成の発光素子(以下、積層型素子という)の態様について、図3を参照して説明する。この発光素子は、第1の電極と第2の電極との間に、複数の発光ユニットを有する発光素子である。発光ユニットとしては、実施の形態2で示した発光物質を含む層と同様な構成を用いることができる。つまり、実施の形態2で示した発光素子は、1つの発光ユニットを有する発光素子であり、本実施の形態では、複数の発光ユニットを有する発光素子について説明する。
本実施の形態では、本発明のキノキサリン誘導体を有機半導体素子の一種である縦型トランジスタ(SIT)の活性層として用いる形態を例示する。
本実施の形態では、本発明のキノキサリン誘導体を用いて作製された発光装置について説明する。
本実施の形態では、実施の形態7に示す発光装置をその一部に含む本発明の電子機器について説明する。本発明の電子機器は、実施の形態1に示したキノキサリン誘導体を含み、熱的安定性が高い表示部を有する。また、長寿命の表示部を有する。また、消費電力の低減された表示部を有する。
2−(4−ブロモフェニル)−3−フェニルキノキサリンの合成方法について説明する。
(4−ブロモフェニル)フェニルアセチレンの合成スキームを(C−1)に示す。
1−(4−ブロモフェニル)−2−フェニルエタンジオンの合成スキームを(C−2)に示す。
2−(4−ブロモフェニル)−3−フェニルキノキサリンの合成スキームを(C−3)に示す。
4−(カルバゾール−9−イル)−ジフェニルアミン(略称:YGA)の合成方法について説明する。
N−(4−ブロモフェニル)カルバゾールの合成スキームを(C−4)に示す。
YGAの合成スキームを(C−5)に示す。
4−(カルバゾール−9−イル)−4’−(3−フェニルキノキサリン−2−イル)トリフェニルアミン(略称:YGA1PQ)の合成
4−(カルバゾール−9−イル)−4’−(3−フェニルキノキサリン−2−イル)トリフェニルアミン(略称:YGA1PQ)の合成スキームを(C−6)に示す。
2,3−ビス(4−ブロモフェニル)キノキサリンの合成方法について説明する。2,3−ビス(4−ブロモフェニル)キノキサリンの合成スキームを(D−1)に示す。
4,4’−(キノキサリン−2,3−ジイル)ビス{N−[4−(9−カルバゾリル)フェニル]−N−フェニルベンゼンアミン}(略称:YGAPQ)の合成方法について説明する。4,4’−(キノキサリン−2,3−ジイル)ビス{N−[4−(9−カルバゾリル)フェニル]−N−フェニルベンゼンアミン}(略称:YGAPQ)の合成スキームを(D−2)に示す。
N−フェニル−(9−フェニルカルバゾール−3−イル)アミン(略称:PCA)の合成方法について説明する。
3−ブロモ−9−フェニルカルバゾールの合成スキームを(E−1)に示す。
PCAの合成スキームを(E−2)に示す。
N,N’−(キノキサリン−2,3−ジイルジ−4,1−フェニレン)ビス(N−フェニル−9−フェニルカルバゾール−3−アミン)(略称:PCAPQ)の合成スキームを(E−3)に示す。
まず、ガラス基板2101上に、酸化珪素を含むインジウム錫酸化物をスパッタリング法にて成膜し、第1の電極2102を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
発光層2105として、4,4’−ジ(N−カルバゾリル)ビフェニル(略称:CBP)と(アセチルアセトナト)ビス(2,3,5−トリフェニルピラジナト)イリジウム(III)(略称:Ir(tppr)2(acac))とを共蒸着することにより、30nmの膜厚で形成した。ここで、CBPとIr(tppr)2(acac)との重量比は、1:0.05(=CBP:Ir(tppr)2(acac))となるように調節した。発光層以外は、発光素子1と同様に形成した。
まず、ガラス基板2101上に、酸化珪素を含むインジウム錫酸化物をスパッタリング法にて成膜し、第1の電極2102を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
電子輸送層2106として、トリス(8−キノリノラト)アルミニウム(略称:Alq)を10nmの膜厚となるように成膜した。電子輸送層以外は、発光素子3と同様に形成した。
まず、ガラス基板2101上に、酸化珪素を含むインジウム錫酸化物をスパッタリング法にて成膜し、第1の電極2102を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
N−フェニル−N−[4−(3−フェニルキノキサリン−2−イル)フェニル]−9−フェニルカルバゾール−3−アミン(略称:PCA1PQ)の合成
N−フェニル−N−[4−(3−フェニルキノキサリン−2−イル)フェニル]−9−フェニルカルバゾール−3−アミン(略称:PCA1PQ)の合成スキームを(H−1)に示す。
N,N’,N’−トリフェニル−N−[4−(3−フェニルキノキサリン−2−イル)フェニル]ベンゼン−1,4−ジアミン(略称:DPA1PQ)の合成
N,N’,N’−トリフェニル−N−[4−(3−フェニルキノキサリン−2−イル)フェニル]ベンゼン−1,4−ジアミン(略称:DPA1PQ)の合成スキームを(J−1)に示す。
まず、ガラス基板2101上に、酸化珪素を含むインジウム錫酸化物をスパッタリング法にて成膜し、第1の電極2102を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
まず、ガラス基板2101上に、酸化珪素を含むインジウム錫酸化物をスパッタリング法にて成膜し、第1の電極2102を形成した。なお、その膜厚は110nmとし、電極面積は2mm×2mmとした。
以下では、構造式(402)で表される(アセチルアセトナト)ビス(2,3,5−トリフェニルピラジナト)イリジウム(III)(略称:[Ir(tppr)2(acac)])の合成例を具体的に例示する。
2,3,5−トリフェニルピラジン(略称:Htppr)の合成について説明する。
ジ−μ−クロロ−ビス[ビス(2,3,5−トリフェニルピラジナト)イリジウム(III)](略称:[Ir(tppr)2Cl]2)の合成について説明する。
(アセチルアセトナト)ビス(2,3,5−トリフェニルピラジナト)イリジウム(III)(略称:[Ir(tppr)2(acac)]の合成について説明する。
上述したステップ1で合成した2,3,5−トリフェニルピラジン(略称:Htppr)に関し、ステップ1とは異なる合成方法を例示する。
102 第1の電極
103 第1の層
104 第2の層
105 第3の層
106 第4の層
107 第2の電極
302 第1の電極
303 第1の層
304 第2の層
305 第3の層
306 第4の層
307 第2の電極
501 第1の電極
502 第2の電極
511 第1の発光ユニット
512 第2の発光ユニット
513 電荷発生層
601 ソース側駆動回路
602 画素部
603 ゲート側駆動回路
604 封止基板
605 シール材
607 空間
608 配線
609 FPC(フレキシブルプリントサーキット)
610 素子基板
611 スイッチング用TFT
612 電流制御用TFT
613 第1の電極
614 絶縁物
616 発光物質を含む層
617 第2の電極
618 発光素子
623 nチャネル型TFT
624 pチャネル型TFT
901 筐体
902 液晶層
903 バックライト
904 筐体
905 ドライバIC
906 端子
951 基板
952 電極
953 絶縁層
954 隔壁層
955 発光物質を含む層
956 電極
1201 ソース電極
1202 活性層
1203 ドレイン電極
1204 ゲート電極
2001 筐体
2002 光源
2101 基板
2102 第1の電極
2103 複合材料を含む層
2104 正孔輸送層
2105 発光層
2106 電子輸送層
2107 電子注入層
2108 第2の電極
9101 筐体
9102 支持台
9103 表示部
9104 スピーカー部
9105 ビデオ入力端子
9201 本体
9202 筐体
9203 表示部
9204 キーボード
9205 外部接続ポート
9206 ポインティングデバイス
9401 本体
9402 筐体
9403 表示部
9404 音声入力部
9405 音声出力部
9406 操作キー
9407 外部接続ポート
9408 アンテナ
9501 本体
9502 表示部
9503 筐体
9504 外部接続ポート
9505 リモコン受信部
9506 受像部
9507 バッテリー
9508 音声入力部
9509 操作キー
9510 接眼部
Claims (16)
- 一般式(1)で表されるキノキサリン誘導体。
- 一般式(2)で表されるキノキサリン誘導体。
- 一般式(3)で表されるキノキサリン誘導体。
- 一般式(4)で表されるキノキサリン誘導体。
- 一般式(5)で表されるキノキサリン誘導体。
- 一般式(6)で表されるキノキサリン誘導体。
- 一般式(7)で表されるキノキサリン誘導体。
- 一般式(8)で表されるキノキサリン誘導体。
- 一般式(9)で表されるキノキサリン誘導体。
- 一対の電極間に、
請求項1乃至請求項10のいずれか一項に記載のキノキサリン誘導体を有することを特徴とする発光素子。 - 一対の電極間に発光層を有し、
前記発光層は請求項1乃至請求項10のいずれか一項に記載のキノキサリン誘導体を有することを特徴とする発光素子。 - 一対の電極間に発光層を有し、
前記発光層は請求項1乃至請求項10のいずれか一項に記載のキノキサリン誘導体と蛍光を発光する物質を有することを特徴とする発光素子。 - 一対の電極間に発光層を有し、
前記発光層は請求項1乃至請求項10のいずれか一項に記載のキノキサリン誘導体と燐光を発光する物質を有することを特徴とする発光素子。 - 請求項11乃至請求項14のいずれか一項に記載の発光素子と、前記発光素子の発光を制御する制御手段とを有する発光装置。
- 表示部を有し、
前記表示部は、請求項11乃至請求項14のいずれか一項に記載の発光素子と前記発光素子の発光を制御する制御手段とを備えたことを特徴とする電子機器。
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JP2010254674A (ja) * | 2009-03-31 | 2010-11-11 | Semiconductor Energy Lab Co Ltd | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
KR101787733B1 (ko) * | 2009-03-31 | 2017-10-18 | 가부시키가이샤 한도오따이 에네루기 켄큐쇼 | 퀴녹살린 유도체, 퀴녹살린 유도체를 사용한 발광 소자, 발광 장치, 조명 장치 및 전자 기기 |
JP2015028047A (ja) * | 2009-03-31 | 2015-02-12 | 株式会社半導体エネルギー研究所 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
JP2016065104A (ja) * | 2009-03-31 | 2016-04-28 | 株式会社半導体エネルギー研究所 | キノキサリン誘導体、キノキサリン誘導体を用いた発光素子、発光装置、照明装置及び電子機器 |
JP2020039007A (ja) * | 2011-04-07 | 2020-03-12 | 株式会社半導体エネルギー研究所 | 発光素子 |
JP2013131743A (ja) * | 2011-11-25 | 2013-07-04 | Semiconductor Energy Lab Co Ltd | 発光素子、発光装置、電子機器、照明装置、及び有機化合物 |
WO2014196585A1 (ja) * | 2013-06-05 | 2014-12-11 | 国立大学法人九州大学 | 発光材料、有機発光素子および化合物 |
JPWO2014196585A1 (ja) * | 2013-06-05 | 2017-02-23 | 株式会社Kyulux | 発光材料、有機発光素子および化合物 |
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